2,6-substituted-4-oxyterpene phenol pyridine compound as well as preparation method and application thereof

A technology of oxyterpene phenol pyridine and compound, which is applied in the field of pharmaceutical compounds, can solve problems such as limiting the clinical application of cisplatin, and achieve good anti-tumor cell proliferation activity, high purity, and good stability

Pending Publication Date: 2021-07-23
FUJIAN SANAN SINO SCI PHOTOBIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Toxicity and drug resistance often limit the clinical application of cisplatin

Method used

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  • 2,6-substituted-4-oxyterpene phenol pyridine compound as well as preparation method and application thereof
  • 2,6-substituted-4-oxyterpene phenol pyridine compound as well as preparation method and application thereof
  • 2,6-substituted-4-oxyterpene phenol pyridine compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055]

[0056] Take a 10mL reaction bottle, add CBD (100mg, 0.32mmol), chloride (108.6mg, 0.32mmol), solvent DMF (1mL) in sequence, mix well, remove oxygen, add Cs 2 CO 3 (104 mg, 0.32 mmol), placed in a 90°C oil bath, reacted for 24 hours, TLC detected the completion of the reaction, cooled to room temperature, placed in an ice-water bath, added 1N HCl to the system to adjust the pH to 3-5, and extracted with ether. The organic phases were combined, washed once with saturated sodium bicarbonate, washed once with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and separated by column chromatography (200-300 mesh silica gel; n-hexane: ethyl acetate = 2:1) to obtain the crude product , using (300-400 mesh silica gel; n-hexane: acetone = 2:1) to obtain the target compound (17.6 mg, yield 11%). 1 H NMR (400MHz, CDCl 3 )δ8.59(d, J=5.6Hz, 2H), 7.63(s, 2H), 6.93(d, J=3.3Hz, 2H), 6.73(s, 2H), 4.89(s, 1H), 4.49( s,1H),4.47(s,1H),4.41(t,...

Embodiment 2

[0058]

[0059] Referring to Example 1 for the synthetic steps of compound I-2, the target compound I-2 (17.8 mg, yield 11.6%) was obtained. 1 H NMR (400MHz, CDCl 3 )δ8.57(d, J=5.6Hz, 1H), 7.63(d, J=2.3Hz, 1H), 6.92(dd, J=5.6, 2.5Hz, 1H), 6.59(s, 1H), 6.33( s,1H),6.04(brs,1H),5.46(brs,1H),5.38–5.24(m,1H),4.52(s,1H),4.40(s,1H),3.70–3.55(m,1H) ,2.57–2.41(m,3H),2.30–2.14(m,1H),2.12–1.99(m,1H),1.84–1.63(m,5H),1.57–1.51(m,2H),1.48(s, 3H), 1.41(d, J=6.3Hz, 6H), 1.34–1.26(m, 4H), 0.86(t, J=6.9Hz, 3H). MS(ESI) m / z: 478[M+H] + .

Embodiment 3

[0061]

[0062] Referring to Example 1 for the synthetic steps of compound I-3, the target compound I-3 (21 mg, yield 13.4%) was obtained. 1 H NMR (400MHz, CDCl 3 )δ8.56(d, J=5.6Hz, 1H), 7.63(d, J=2.3Hz, 1H), 6.93(dd, J=5.5, 2.4Hz, 1H), 6.60(s, 1H), 6.33( s,1H),6.05(brs,1H),5.46(brs,1H),4.51(s,1H),4.41(s,1H),4.39(t,J=6.8Hz,2H),3.70–3.55(m ,1H),2.55–2.43(m,3H),2.29–2.14(m,1H),2.12–1.98(m,1H),1.84–1.63(m,7H),1.59–1.51(m,2H),1.51 –1.37(m,5H),1.34–1.21(m,4H),0.96(t,J=7.4Hz,3H), 0.87(t,J=6.9Hz,3H).MS(ESI)m / z:492 [M+H] + .

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Abstract

The invention discloses a 2,6-substituted-4-oxyterpene phenol pyridine compound as shown in a formula I which is described in the specification and a preparation method and application thereof. The 2,6-substituted-4-oxyterpene phenol pyridine compound is a novel compound and is obtained through synthesis. Cell experiments prove that the compound has good anti-tumor cell proliferation activity and especially has an obvious tumor cell proliferation inhibition effect in liver cancer cells. The compound obtained by the method is high in purity, good in stability and good in biological activity. When the compound is combined with cis-platinum for use, the effect of inhibiting tumor cell proliferation is more obvious.

Description

technical field [0001] The invention relates to a pharmaceutical compound, in particular to a 2,6-substituted-4-oxyterpene phenol pyridine compound and its preparation method and application. Background technique [0002] Cancer (malignant tumor) refers to the disease caused by the abnormal regulation of cell proliferation mechanism. The incidence of cancer is gradually increasing due to different living habits and environmental factors. Common cancer treatment methods include surgery, chemotherapy, radiotherapy, immunotherapy and monoclonal antibody therapy, and chemotherapy is still the most important treatment. The occurrence of tumor multidrug resistance is the main reason leading to the clinical failure of chemotherapy. In order to achieve the purpose of treatment, drug combination is often used clinically, but drug combination often causes interaction of drugs in vivo or in vitro. For certain drug combinations, combination therapy also allows optimal combination dosa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/79C07D213/81A61K31/44A61K33/243A61P35/00A61P35/04
CPCC07D213/79C07D213/81A61K31/44A61K33/243A61P35/00A61P35/04A61K2300/00
Inventor 张婷林祖铭张靖
Owner FUJIAN SANAN SINO SCI PHOTOBIOTECH CO LTD
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